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Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades
Author(s) -
Dauncey Elizabeth M.,
Morcillo Sara P.,
Douglas James J.,
Sheikh Nadeem S.,
Leonori Daniele
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710790
Subject(s) - radical , chemistry , bond cleavage , photochemistry , transposition (logic) , cleavage (geology) , molecule , cascade , photoredox catalysis , combinatorial chemistry , catalysis , organic chemistry , materials science , computer science , photocatalysis , fracture (geology) , composite material , chromatography , artificial intelligence
A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp 3 )−(sp 3 ) and C(sp 3 )−H bond cleavage gives access to distal carbon radicals that undergo S H 2 functionalisations. These mild, visible‐light‐mediated procedures can be used for remote fluorination, chlorination, and azidation, and were applied to the modification of bioactive and structurally complex molecules.